Hydrogen Peroxide → 5-Amino-4-cyano-3-(dimethylamino)isothiazole

HRID 616493Notes

Reaction equation

HRID 616493 reaction equation
[NH2:1][C:2]([N:9]([CH3:11])[CH3:10])=[C:3]([C:7]#[N:8])[C:4](=[S:6])[NH2:5].OO>C(O)C>[NH2:5][C:4]1[S:6][N:1]=[C:2]([N:9]([CH3:10])[CH3:11])[C:3]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 859420223-Amino-2-cyano-3-(dimethylamino)propenethioamide

Product 1

HCID 203675775-Amino-4-cyano-3-(dimethylamino)isothiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A slurry of 5.1 g of 3-amino-2-cyano-3-(dimethylamino)propenethioamide and 25 ml of ethanol was heated to reflux (about 80°) while 3.8 ml of 30% hydrogen peroxide (1.1 g of active H2O2) were added dropwise; the exothermic reaction maintained the mixture at the reflux temperature. After addition of the peroxide was completed, the reaction mixture was heated under reflux for 30 minutes, then filtered hot and allowed to cool. The mixture was diluted with 100 ml of water and stirred for 15 minutes. The resulting precipitate, 5-amino-4-cyano-3-(dimethylamino)isothiazole, was collected by filtration.

Workup

  1. additionwere added dropwise
  2. customthe exothermic reaction
  3. temperaturemaintained the mixture at the reflux temperature
  4. temperaturethe reaction mixture was heated
  5. temperatureunder reflux for 30 minutes
  6. filtrationfiltered hot
  7. temperatureto cool
  8. additionThe mixture was diluted with 100 ml of water
  9. filtrationThe resulting precipitate, 5-amino-4-cyano-3-(dimethylamino)isothiazole, was collected by filtration

Sources & evidence

ORD record
ord-a7638944eff6479b8665d4fbd7656c64
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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